This is Tableau server, I'm not sure what caching is set to...or how to check that? When I manually go in and refresh extracts, everything updates in the workbook. The CSV file I'm connecting to is updating.

Sharad Adhikari hit it on the nose. you need to uncheck include external files and the csv needs to be in a location that Tableau server can reach. (network drive or something)

when you include external files, it uploads the csv, in the state at the time of publish, and uses that going forward.

if the csv is on your computer, you need to move it to a network location or network share, and when you connect to it in desktop you need to use the UNC path (i.e. \\10.xxx.yyy.zzz\tableau files\data\mydata.csv rather than Z:\\data\mydata.csv)

Not sure how you derived they're confused. I too have a similar issue and the workbook is pointed to a published data source that Tableau Bridge maintains. The workbook simply doesn't show new information unless you manually force it to, but the data source is updated and DOES contain the information.

what are your caching settings set to? if Tableau server is set to "cache less often" tableau will use the data from the last time the view was loaded, even if the published data source has refreshed, if you force refresh the view then it will re-query the data source regardless. once you have gotten passed what ever the cache life is set to (12hr for example) the view will do a full refresh on it's own. I think this behavior is to try to balance load time against data update frequency